5-fluoro-2,3-dihydro-1H-isoindol-1-one → 5-(Ethyl(methyl)amino)isoindolin-1-one
Reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2>C(O)C>[CH2:5]([N:6]([CH3:7])[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2)[CH3:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 165 °C
Procedure
A 500-mL high-pressure bomb reactor was charged with 106b (539 mg, 3.57 mmol), ethanol (30 mL) and excess N,N-ethylmethylamine (50 mL). The mixture was heated at 165° C. for 36 h. After this time, the mixture was concentrated and the resulting residue was purified by flash column chromatography (silica, 98:2 ethyl acetate/triethyl-amine) to afford 106c in 59% yield (397 mg) as a yellow solid: mp 127-129° C.; 1H NMR (500 MHz, DMSO-d6) δ 7.93 (s, 1H), 7.42 (dd, J=7.0, 2.5 Hz, 1H), 6.77-6.75 (m, 2H), 4.23 (s, 2H), 3.46 (q, J=7.0 Hz, 2H), 2.94 (s, 3H), 1.06 (t, J=7.0 Hz, 3H); MS (ESI+) m/z 191.1 (M+H).
Workup
- concentrationAfter this time, the mixture was concentrated
- customthe resulting residue was purified by flash column chromatography (silica, 98:2 ethyl acetate/triethyl-amine)
Sources & evidence
- ORD record
- ord-b9e29248312b43eb84cb34ebe5cfc00a
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975260B2
Reaction notes
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